diff --git a/certbot-ci/src/certbot_integration_tests/certbot_tests/assertions.py b/certbot-ci/src/certbot_integration_tests/certbot_tests/assertions.py
index 9b0672a01..69582fba5 100644
--- a/certbot-ci/src/certbot_integration_tests/certbot_tests/assertions.py
+++ b/certbot-ci/src/certbot_integration_tests/certbot_tests/assertions.py
@@ -1,7 +1,6 @@
 """This module contains advanced assertions for the certbot integration tests."""
 import os
 from typing import Optional
-from typing import Type
 
 from cryptography.hazmat.backends import default_backend
 from cryptography.hazmat.primitives.asymmetric.ec import EllipticCurve
@@ -22,7 +21,7 @@ SYSTEM_SID = 'S-1-5-18'
 ADMINS_SID = 'S-1-5-32-544'
 
 
-def assert_elliptic_key(key_path: str, curve: Type[EllipticCurve]) -> None:
+def assert_elliptic_key(key_path: str, curve: type[EllipticCurve]) -> None:
     """
     Asserts that the key at the given path is an EC key using the given curve.
     :param key_path: path to key
diff --git a/certbot-ci/src/certbot_integration_tests/certbot_tests/context.py b/certbot-ci/src/certbot_integration_tests/certbot_tests/context.py
index 4a998c171..7c2672e6f 100644
--- a/certbot-ci/src/certbot_integration_tests/certbot_tests/context.py
+++ b/certbot-ci/src/certbot_integration_tests/certbot_tests/context.py
@@ -4,7 +4,6 @@ import shutil
 import sys
 import tempfile
 from typing import Iterable
-from typing import Tuple
 
 import pytest
 
@@ -67,7 +66,7 @@ class IntegrationTestsContext:
         """Cleanup the integration test context."""
         shutil.rmtree(self.workspace)
 
-    def certbot(self, args: Iterable[str], force_renew: bool = True) -> Tuple[str, str]:
+    def certbot(self, args: Iterable[str], force_renew: bool = True) -> tuple[str, str]:
         """
         Execute certbot with given args, not renewing certificates by default.
         :param args: args to pass to certbot
diff --git a/certbot-ci/src/certbot_integration_tests/certbot_tests/test_main.py b/certbot-ci/src/certbot_integration_tests/certbot_tests/test_main.py
index 2b4ea2a2f..a240f70a8 100644
--- a/certbot-ci/src/certbot_integration_tests/certbot_tests/test_main.py
+++ b/certbot-ci/src/certbot_integration_tests/certbot_tests/test_main.py
@@ -8,8 +8,6 @@ import shutil
 import subprocess
 import time
 from typing import Generator
-from typing import Tuple
-from typing import Type
 
 from cryptography.hazmat.primitives.asymmetric.ec import EllipticCurve
 from cryptography.hazmat.primitives.asymmetric.ec import SECP256R1
@@ -570,7 +568,7 @@ def test_reuse_key_allow_subset_of_names(context: IntegrationTestsContext) -> No
 
 def test_new_key(context: IntegrationTestsContext) -> None:
     """Tests --new-key and its interactions with --reuse-key"""
-    def private_key(generation: int) -> Tuple[str, str]:
+    def private_key(generation: int) -> tuple[str, str]:
         pk_path = join(context.config_dir, f'archive/{certname}/privkey{generation}.pem')
         with open(pk_path, 'r') as file:
             return file.read(), pk_path
@@ -670,7 +668,7 @@ def test_default_rsa_size(context: IntegrationTestsContext) -> None:
     ('secp521r1', SECP521R1)]
 )
 def test_ecdsa_curves(context: IntegrationTestsContext, curve: str,
-                      curve_cls: Type[EllipticCurve]) -> None:
+                      curve_cls: type[EllipticCurve]) -> None:
     """Test issuance for each supported ECDSA curve"""
     domain = context.get_domain('curve')
     context.certbot([
@@ -806,7 +804,7 @@ def test_revoke_and_unregister(context: IntegrationTestsContext) -> None:
     ('secp521r1', SECP521R1)]
 )
 def test_revoke_ecdsa_cert_key(
-    context: IntegrationTestsContext, curve: str, curve_cls: Type[EllipticCurve]) -> None:
+    context: IntegrationTestsContext, curve: str, curve_cls: type[EllipticCurve]) -> None:
     """Test revoking a certificate """
     cert: str = context.get_domain('curve')
     context.certbot([
@@ -831,7 +829,7 @@ def test_revoke_ecdsa_cert_key(
     ('secp521r1', SECP521R1)]
 )
 def test_revoke_ecdsa_cert_key_delete(
-    context: IntegrationTestsContext, curve: str, curve_cls: Type[EllipticCurve]) -> None:
+    context: IntegrationTestsContext, curve: str, curve_cls: type[EllipticCurve]) -> None:
     """Test revoke and deletion for each supported curve type"""
     cert: str = context.get_domain('curve')
     context.certbot([
diff --git a/certbot-ci/src/certbot_integration_tests/nginx_tests/context.py b/certbot-ci/src/certbot_integration_tests/nginx_tests/context.py
index 54a3c0164..282dda61a 100644
--- a/certbot-ci/src/certbot_integration_tests/nginx_tests/context.py
+++ b/certbot-ci/src/certbot_integration_tests/nginx_tests/context.py
@@ -2,7 +2,6 @@
 import os
 import subprocess
 from typing import Iterable
-from typing import Tuple
 
 import pytest
 
@@ -36,7 +35,7 @@ class IntegrationTestsContext(certbot_context.IntegrationTestsContext):
         self._stop_nginx()
         super().cleanup()
 
-    def certbot_test_nginx(self, args: Iterable[str]) -> Tuple[str, str]:
+    def certbot_test_nginx(self, args: Iterable[str]) -> tuple[str, str]:
         """
         Main command to execute certbot using the nginx plugin.
         :param list args: list of arguments to pass to nginx
diff --git a/certbot-ci/src/certbot_integration_tests/nginx_tests/test_main.py b/certbot-ci/src/certbot_integration_tests/nginx_tests/test_main.py
index b2cc0f5b5..099d79989 100644
--- a/certbot-ci/src/certbot_integration_tests/nginx_tests/test_main.py
+++ b/certbot-ci/src/certbot_integration_tests/nginx_tests/test_main.py
@@ -2,7 +2,6 @@
 import os
 import ssl
 from typing import Generator
-from typing import List
 
 import pytest
 
@@ -33,7 +32,7 @@ def test_context(request: pytest.FixtureRequest) -> Generator[IntegrationTestsCo
         '--preferred-challenges', 'http'
     ], {'default_server': False}),
 ], indirect=['context'])
-def test_certificate_deployment(certname_pattern: str, params: List[str],
+def test_certificate_deployment(certname_pattern: str, params: list[str],
                                 context: IntegrationTestsContext) -> None:
     """
     Test various scenarios to deploy a certificate to nginx using certbot.
diff --git a/certbot-ci/src/certbot_integration_tests/rfc2136_tests/context.py b/certbot-ci/src/certbot_integration_tests/rfc2136_tests/context.py
index 056f1d8a2..12cb65cc7 100644
--- a/certbot-ci/src/certbot_integration_tests/rfc2136_tests/context.py
+++ b/certbot-ci/src/certbot_integration_tests/rfc2136_tests/context.py
@@ -4,7 +4,6 @@ import importlib.resources
 import tempfile
 from typing import Generator
 from typing import Iterable
-from typing import Tuple
 
 import pytest
 
@@ -24,7 +23,7 @@ class IntegrationTestsContext(certbot_context.IntegrationTestsContext):
         else:  # Primary node
             self._dns_xdist = request.config.dns_xdist  # type: ignore[attr-defined]
 
-    def certbot_test_rfc2136(self, args: Iterable[str]) -> Tuple[str, str]:
+    def certbot_test_rfc2136(self, args: Iterable[str]) -> tuple[str, str]:
         """
         Main command to execute certbot using the RFC2136 DNS authenticator.
         :param list args: list of arguments to pass to Certbot
diff --git a/certbot-ci/src/certbot_integration_tests/utils/acme_server.py b/certbot-ci/src/certbot_integration_tests/utils/acme_server.py
index b196fa8c6..bb1cec976 100755
--- a/certbot-ci/src/certbot_integration_tests/utils/acme_server.py
+++ b/certbot-ci/src/certbot_integration_tests/utils/acme_server.py
@@ -13,11 +13,8 @@ import time
 from types import TracebackType
 from typing import Any
 from typing import cast
-from typing import Dict
-from typing import List
 from typing import Mapping
 from typing import Optional
-from typing import Type
 
 # pylint: disable=wildcard-import,unused-wildcard-import
 from certbot_integration_tests.utils import misc
@@ -44,7 +41,7 @@ class ACMEServer:
     ACMEServer is also a context manager, and so can be used to ensure ACME server is
     started/stopped upon context enter/exit.
     """
-    def __init__(self, nodes: List[str], http_proxy: bool = True,
+    def __init__(self, nodes: list[str], http_proxy: bool = True,
                  stdout: bool = False, dns_server: Optional[str] = None,
                  http_01_port: Optional[int] = None) -> None:
         """
@@ -60,7 +57,7 @@ class ACMEServer:
 
         self._proxy = http_proxy
         self._workspace = tempfile.mkdtemp()
-        self._processes: List[subprocess.Popen[bytes]] = []
+        self._processes: list[subprocess.Popen[bytes]] = []
         self._stdout = sys.stdout if stdout else open(os.devnull, 'w') # pylint: disable=consider-using-with
         self._dns_server = dns_server
         self._http_01_port = DEFAULT_HTTP_01_PORT
@@ -101,17 +98,17 @@ class ACMEServer:
             self._stdout.close()
         print('=> Test infrastructure stopped and cleaned up.')
 
-    def __enter__(self) -> Dict[str, Any]:
+    def __enter__(self) -> dict[str, Any]:
         self.start()
         return self.acme_xdist
 
-    def __exit__(self, exc_type: Optional[Type[BaseException]], exc: Optional[BaseException],
+    def __exit__(self, exc_type: Optional[type[BaseException]], exc: Optional[BaseException],
                  traceback: Optional[TracebackType]) -> None:
         self.stop()
 
-    def _construct_acme_xdist(self, nodes: List[str]) -> None:
+    def _construct_acme_xdist(self, nodes: list[str]) -> None:
         """Generate and return the acme_xdist dict"""
-        acme_xdist: Dict[str, Any] = {}
+        acme_xdist: dict[str, Any] = {}
 
         # Directory and ACME port are set implicitly in the docker-compose.yml
         # files of Pebble.
@@ -161,14 +158,14 @@ class ACMEServer:
     def _prepare_http_proxy(self) -> None:
         """Configure and launch an HTTP proxy"""
         print(f'=> Configuring the HTTP proxy on port {self._http_01_port}...')
-        http_port_map = cast(Dict[str, int], self.acme_xdist['http_port'])
+        http_port_map = cast(dict[str, int], self.acme_xdist['http_port'])
         mapping = {r'.+\.{0}\.wtf'.format(node): 'http://127.0.0.1:{0}'.format(port)
                    for node, port in http_port_map.items()}
         command = [sys.executable, proxy.__file__, str(self._http_01_port), json.dumps(mapping)]
         self._launch_process(command)
         print('=> Finished configuring the HTTP proxy.')
 
-    def _launch_process(self, command: List[str], cwd: str = os.getcwd(),
+    def _launch_process(self, command: list[str], cwd: str = os.getcwd(),
                         env: Optional[Mapping[str, str]] = None,
                         force_stderr: bool = False) -> subprocess.Popen[bytes]:
         """Launch silently a subprocess OS command"""
diff --git a/certbot-ci/src/certbot_integration_tests/utils/certbot_call.py b/certbot-ci/src/certbot_integration_tests/utils/certbot_call.py
index 2fc6021a7..7edf12a51 100755
--- a/certbot-ci/src/certbot_integration_tests/utils/certbot_call.py
+++ b/certbot-ci/src/certbot_integration_tests/utils/certbot_call.py
@@ -4,10 +4,7 @@
 import os
 import subprocess
 import sys
-from typing import Dict
-from typing import List
 from typing import Optional
-from typing import Tuple
 
 import certbot_integration_tests
 from certbot_integration_tests.utils.constants import DEFAULT_HTTP_01_PORT
@@ -15,9 +12,9 @@ from certbot_integration_tests.utils.constants import HTTPS_PORT
 from certbot_integration_tests.utils.constants import PEBBLE_DIRECTORY_URL
 
 
-def certbot_test(certbot_args: List[str], directory_url: Optional[str], http_01_port: int,
+def certbot_test(certbot_args: list[str], directory_url: Optional[str], http_01_port: int,
                  https_port: int, config_dir: str, workspace: str,
-                 force_renew: bool = True) -> Tuple[str, str]:
+                 force_renew: bool = True) -> tuple[str, str]:
     """
     Invoke the certbot executable available in PATH in a test context for the given args.
     The test context consists in running certbot in debug mode, with various flags suitable
@@ -45,7 +42,7 @@ def certbot_test(certbot_args: List[str], directory_url: Optional[str], http_01_
     return proc.stdout, proc.stderr
 
 
-def _prepare_environ(workspace: str) -> Dict[str, str]:
+def _prepare_environ(workspace: str) -> dict[str, str]:
     # pylint: disable=missing-function-docstring
 
     new_environ = os.environ.copy()
@@ -83,9 +80,9 @@ def _prepare_environ(workspace: str) -> Dict[str, str]:
     return new_environ
 
 
-def _prepare_args_env(certbot_args: List[str], directory_url: Optional[str], http_01_port: int,
+def _prepare_args_env(certbot_args: list[str], directory_url: Optional[str], http_01_port: int,
                       https_port: int, config_dir: str, workspace: str,
-                      force_renew: bool) -> Tuple[List[str], Dict[str, str]]:
+                      force_renew: bool) -> tuple[list[str], dict[str, str]]:
 
     new_environ = _prepare_environ(workspace)
     additional_args = ['--no-random-sleep-on-renew']
diff --git a/certbot-ci/src/certbot_integration_tests/utils/dns_server.py b/certbot-ci/src/certbot_integration_tests/utils/dns_server.py
index b13f0fd48..657ce6bd6 100644
--- a/certbot-ci/src/certbot_integration_tests/utils/dns_server.py
+++ b/certbot-ci/src/certbot_integration_tests/utils/dns_server.py
@@ -11,10 +11,7 @@ import tempfile
 import time
 from types import TracebackType
 from typing import Any
-from typing import Dict
-from typing import List
 from typing import Optional
-from typing import Type
 
 from certbot_integration_tests.utils import constants
 
@@ -36,7 +33,7 @@ class DNSServer:
     future to support parallelization (https://github.com/certbot/certbot/issues/8455).
     """
 
-    def __init__(self, unused_nodes: List[str], show_output: bool = False) -> None:
+    def __init__(self, unused_nodes: list[str], show_output: bool = False) -> None:
         """
         Create an DNSServer instance.
         :param list nodes: list of node names that will be setup by pytest xdist
@@ -155,10 +152,10 @@ class DNSServer:
             "Gave up waiting for DNS server {} to respond".format(BIND_BIND_ADDRESS)
         )
 
-    def __start__(self) -> Dict[str, Any]:
+    def __start__(self) -> dict[str, Any]:
         self.start()
         return self.dns_xdist
 
-    def __exit__(self, exc_type: Optional[Type[BaseException]], exc: Optional[BaseException],
+    def __exit__(self, exc_type: Optional[type[BaseException]], exc: Optional[BaseException],
                  traceback: Optional[TracebackType]) -> None:
         self.stop()
diff --git a/certbot-ci/src/certbot_integration_tests/utils/misc.py b/certbot-ci/src/certbot_integration_tests/utils/misc.py
index 34687d9e8..bac6bd7eb 100644
--- a/certbot-ci/src/certbot_integration_tests/utils/misc.py
+++ b/certbot-ci/src/certbot_integration_tests/utils/misc.py
@@ -20,9 +20,7 @@ import threading
 import time
 from typing import Generator
 from typing import Iterable
-from typing import List
 from typing import Optional
-from typing import Tuple
 from typing import Union
 
 from cryptography import x509
@@ -103,7 +101,7 @@ def create_http_server(port: int) -> Generator[str, None, None]:
             server.server_close()
 
 
-def list_renewal_hooks_dirs(config_dir: str) -> List[str]:
+def list_renewal_hooks_dirs(config_dir: str) -> list[str]:
     """
     Find and return paths of all hook directories for the given certbot config directory
     :param str config_dir: path to the certbot config directory
@@ -159,7 +157,7 @@ set -e
 
 
 @contextlib.contextmanager
-def manual_http_hooks(http_server_root: str) -> Generator[Tuple[str, str], None, None]:
+def manual_http_hooks(http_server_root: str) -> Generator[tuple[str, str], None, None]:
     """
     Generate suitable http-01 hooks command for test purpose in the given HTTP
     server webroot directory. These hooks command use temporary python scripts
@@ -303,7 +301,7 @@ def echo(keyword: str, path: Optional[str] = None) -> str:
         os.path.basename(sys.executable), keyword, ' >> "{0}"'.format(path) if path else '')
 
 
-def get_acme_issuers() -> List[Certificate]:
+def get_acme_issuers() -> list[Certificate]:
     """Gets the list of one or more issuer certificates from the ACME server used by the
     context.
     :param context: the testing context.
diff --git a/certbot-ci/src/certbot_integration_tests/utils/pebble_artifacts.py b/certbot-ci/src/certbot_integration_tests/utils/pebble_artifacts.py
index bb504bfaa..de9956847 100644
--- a/certbot-ci/src/certbot_integration_tests/utils/pebble_artifacts.py
+++ b/certbot-ci/src/certbot_integration_tests/utils/pebble_artifacts.py
@@ -8,7 +8,7 @@ import platform
 import stat
 import zipfile
 from contextlib import ExitStack
-from typing import Optional, Tuple
+from typing import Optional
 
 import requests
 
@@ -18,7 +18,7 @@ from certbot_integration_tests.utils.constants import MOCK_OCSP_SERVER_PORT
 PEBBLE_VERSION = 'v2.8.0'
 
 
-def fetch(workspace: str, http_01_port: int = DEFAULT_HTTP_01_PORT) -> Tuple[str, str, str]:
+def fetch(workspace: str, http_01_port: int = DEFAULT_HTTP_01_PORT) -> tuple[str, str, str]:
     # pylint: disable=missing-function-docstring
     file_manager = ExitStack()
     atexit.register(file_manager.close)
diff --git a/certbot-ci/src/certbot_integration_tests/utils/proxy.py b/certbot-ci/src/certbot_integration_tests/utils/proxy.py
index ba53381e6..4960ec93e 100644
--- a/certbot-ci/src/certbot_integration_tests/utils/proxy.py
+++ b/certbot-ci/src/certbot_integration_tests/utils/proxy.py
@@ -6,14 +6,13 @@ import json
 import re
 import sys
 from typing import Mapping
-from typing import Type
 
 import requests
 
 from certbot_integration_tests.utils.misc import GracefulTCPServer
 
 
-def _create_proxy(mapping: Mapping[str, str]) -> Type[BaseHTTPServer.BaseHTTPRequestHandler]:
+def _create_proxy(mapping: Mapping[str, str]) -> type[BaseHTTPServer.BaseHTTPRequestHandler]:
     # pylint: disable=missing-function-docstring
     class ProxyHandler(BaseHTTPServer.BaseHTTPRequestHandler):
         # pylint: disable=missing-class-docstring
diff --git a/certbot-compatibility-test/src/certbot_compatibility_test/configurators/apache/common.py b/certbot-compatibility-test/src/certbot_compatibility_test/configurators/apache/common.py
index 1aecbf523..ff7115571 100644
--- a/certbot-compatibility-test/src/certbot_compatibility_test/configurators/apache/common.py
+++ b/certbot-compatibility-test/src/certbot_compatibility_test/configurators/apache/common.py
@@ -3,8 +3,6 @@ import argparse
 import os
 import shutil
 import subprocess
-from typing import Set
-from typing import Tuple
 from unittest import mock
 
 from certbot import configuration
@@ -80,7 +78,7 @@ def _get_server_root(config: str) -> str:
     return os.path.join(config, subdirs[0].rstrip())
 
 
-def _get_names(config: str) -> Tuple[Set[str], Set[str]]:
+def _get_names(config: str) -> tuple[set[str], set[str]]:
     """Returns all and testable domain names in config"""
     all_names = set()
     non_ip_names = set()
diff --git a/certbot-compatibility-test/src/certbot_compatibility_test/configurators/common.py b/certbot-compatibility-test/src/certbot_compatibility_test/configurators/common.py
index 44a1cec01..d22422dc0 100644
--- a/certbot-compatibility-test/src/certbot_compatibility_test/configurators/common.py
+++ b/certbot-compatibility-test/src/certbot_compatibility_test/configurators/common.py
@@ -6,12 +6,8 @@ import os
 import shutil
 import tempfile
 from typing import Iterable
-from typing import List
 from typing import Optional
 from typing import overload
-from typing import Set
-from typing import Tuple
-from typing import Type
 from typing import Union
 
 from acme import challenges
@@ -50,8 +46,8 @@ class Proxy(interfaces.ConfiguratorProxy):
         self.http_port = 80
         self.https_port = 443
         self._configurator: common.Configurator
-        self._all_names: Optional[Set[str]] = None
-        self._test_names: Optional[Set[str]] = None
+        self._all_names: Optional[set[str]] = None
+        self._test_names: Optional[set[str]] = None
 
     def has_more_configs(self) -> bool:
         """Returns true if there are more configs to test"""
@@ -70,14 +66,14 @@ class Proxy(interfaces.ConfiguratorProxy):
 
     @overload
     def copy_certs_and_keys(self, cert_path: str, key_path: str,
-                            chain_path: str) -> Tuple[str, str, str]: ...
+                            chain_path: str) -> tuple[str, str, str]: ...
 
     @overload
     def copy_certs_and_keys(self, cert_path: str, key_path: str,
-                            chain_path: Optional[str]) -> Tuple[str, str, Optional[str]]: ...
+                            chain_path: Optional[str]) -> tuple[str, str, Optional[str]]: ...
 
     def copy_certs_and_keys(self, cert_path: str, key_path: str,
-                            chain_path: Optional[str] = None) -> Tuple[str, str, Optional[str]]:
+                            chain_path: Optional[str] = None) -> tuple[str, str, Optional[str]]:
         """Copies certs and keys into the temporary directory"""
         cert_and_key_dir = os.path.join(self._temp_dir, "certs_and_keys")
         if not os.path.isdir(cert_and_key_dir):
@@ -94,13 +90,13 @@ class Proxy(interfaces.ConfiguratorProxy):
 
         return cert, key, chain
 
-    def get_all_names_answer(self) -> Set[str]:
+    def get_all_names_answer(self) -> set[str]:
         """Returns the set of domain names that the plugin should find"""
         if self._all_names:
             return self._all_names
         raise errors.Error("No configuration file loaded")
 
-    def get_testable_domain_names(self) -> Set[str]:
+    def get_testable_domain_names(self) -> set[str]:
         """Returns the set of domain names that can be tested against"""
         if self._test_names:
             return self._test_names
@@ -115,20 +111,20 @@ class Proxy(interfaces.ConfiguratorProxy):
         self._configurator.deploy_cert(
             domain, cert_path, key_path, chain_path, fullchain_path)
 
-    def cleanup(self, achalls: List[AnnotatedChallenge]) -> None:
+    def cleanup(self, achalls: list[AnnotatedChallenge]) -> None:
         self._configurator.cleanup(achalls)
 
     def config_test(self) -> None:
         self._configurator.config_test()
 
     def enhance(self, domain: str, enhancement: str,
-                options: Optional[Union[List[str], str]] = None) -> None:
+                options: Optional[Union[list[str], str]] = None) -> None:
         self._configurator.enhance(domain, enhancement, options)
 
     def get_all_names(self) -> Iterable[str]:
         return self._configurator.get_all_names()
 
-    def get_chall_pref(self, domain: str) -> Iterable[Type[Challenge]]:
+    def get_chall_pref(self, domain: str) -> Iterable[type[Challenge]]:
         return self._configurator.get_chall_pref(domain)
 
     @classmethod
@@ -138,7 +134,7 @@ class Proxy(interfaces.ConfiguratorProxy):
     def more_info(self) -> str:
         return self._configurator.more_info()
 
-    def perform(self, achalls: List[AnnotatedChallenge]) -> List[challenges.ChallengeResponse]:
+    def perform(self, achalls: list[AnnotatedChallenge]) -> list[challenges.ChallengeResponse]:
         return self._configurator.perform(achalls)
 
     def prepare(self) -> None:
@@ -156,5 +152,5 @@ class Proxy(interfaces.ConfiguratorProxy):
     def save(self, title: Optional[str] = None, temporary: bool = False) -> None:
         self._configurator.save(title, temporary)
 
-    def supported_enhancements(self) -> List[str]:
+    def supported_enhancements(self) -> list[str]:
         return self._configurator.supported_enhancements()
diff --git a/certbot-compatibility-test/src/certbot_compatibility_test/configurators/nginx/common.py b/certbot-compatibility-test/src/certbot_compatibility_test/configurators/nginx/common.py
index 6f2b9c1ae..ddfc82c77 100644
--- a/certbot-compatibility-test/src/certbot_compatibility_test/configurators/nginx/common.py
+++ b/certbot-compatibility-test/src/certbot_compatibility_test/configurators/nginx/common.py
@@ -2,8 +2,6 @@
 import os
 import shutil
 import subprocess
-from typing import Set
-from typing import Tuple
 
 from certbot import configuration
 from certbot_compatibility_test import errors
@@ -64,9 +62,9 @@ def _get_server_root(config: str) -> str:
     return os.path.join(config, subdirs[0].rstrip())
 
 
-def _get_names(config: str) -> Tuple[Set[str], Set[str]]:
+def _get_names(config: str) -> tuple[set[str], set[str]]:
     """Returns all and testable domain names in config"""
-    all_names: Set[str] = set()
+    all_names: set[str] = set()
     for root, _dirs, files in os.walk(config):
         for this_file in files:
             update_names = _get_server_names(root, this_file)
@@ -75,7 +73,7 @@ def _get_names(config: str) -> Tuple[Set[str], Set[str]]:
     return all_names, non_ip_names
 
 
-def _get_server_names(root: str, filename: str) -> Set[str]:
+def _get_server_names(root: str, filename: str) -> set[str]:
     """Returns all names in a config file path"""
     all_names = set()
     with open(os.path.join(root, filename)) as f:
diff --git a/certbot-compatibility-test/src/certbot_compatibility_test/interfaces.py b/certbot-compatibility-test/src/certbot_compatibility_test/interfaces.py
index ae8eeffca..a47a85ae2 100644
--- a/certbot-compatibility-test/src/certbot_compatibility_test/interfaces.py
+++ b/certbot-compatibility-test/src/certbot_compatibility_test/interfaces.py
@@ -3,7 +3,6 @@ from abc import ABCMeta
 from abc import abstractmethod
 import argparse
 from typing import cast
-from typing import Set
 
 from certbot import interfaces
 from certbot.configuration import NamespaceConfig
@@ -45,7 +44,7 @@ class PluginProxy(interfaces.Plugin, metaclass=ABCMeta):
         """Loads the next config and returns its name"""
 
     @abstractmethod
-    def get_testable_domain_names(self) -> Set[str]:
+    def get_testable_domain_names(self) -> set[str]:
         """Returns the domain names that can be used in testing"""
 
 
@@ -57,7 +56,7 @@ class InstallerProxy(PluginProxy, interfaces.Installer, metaclass=ABCMeta):
     """Wraps a Certbot installer"""
 
     @abstractmethod
-    def get_all_names_answer(self) -> Set[str]:
+    def get_all_names_answer(self) -> set[str]:
         """Returns all names that should be found by the installer"""
 
 
diff --git a/certbot-compatibility-test/src/certbot_compatibility_test/test_driver.py b/certbot-compatibility-test/src/certbot_compatibility_test/test_driver.py
index 791b6f1f6..d5e661d2b 100644
--- a/certbot-compatibility-test/src/certbot_compatibility_test/test_driver.py
+++ b/certbot-compatibility-test/src/certbot_compatibility_test/test_driver.py
@@ -10,13 +10,9 @@ import sys
 import tempfile
 import time
 from typing import Any
-from typing import Dict
 from typing import Generator
 from typing import Iterable
-from typing import List
 from typing import Optional
-from typing import Tuple
-from typing import Type
 
 from cryptography.hazmat.primitives import serialization
 from urllib3.util import connection
@@ -42,7 +38,7 @@ tests that the plugin supports are performed.
 
 """
 
-PLUGINS: Dict[str, Type[common.Proxy]] = {"apache": a_common.Proxy, "nginx": n_common.Proxy}
+PLUGINS: dict[str, type[common.Proxy]] = {"apache": a_common.Proxy, "nginx": n_common.Proxy}
 
 
 logger = logging.getLogger(__name__)
@@ -103,9 +99,9 @@ def test_authenticator(plugin: common.Proxy, config: str, temp_dir: str) -> bool
     return success
 
 
-def _create_achalls(plugin: common.Proxy) -> List[achallenges.AnnotatedChallenge]:
+def _create_achalls(plugin: common.Proxy) -> list[achallenges.AnnotatedChallenge]:
     """Returns a list of annotated challenges to test on plugin"""
-    achalls: List[achallenges.AnnotatedChallenge] = []
+    achalls: list[achallenges.AnnotatedChallenge] = []
     names = plugin.get_testable_domain_names()
     for domain in names:
         prefs = plugin.get_chall_pref(domain)
@@ -145,7 +141,7 @@ def test_installer(args: argparse.Namespace, plugin: common.Proxy, config: str,
     return names_match and success and good_rollback
 
 
-def test_deploy_cert(plugin: common.Proxy, temp_dir: str, domains: List[str]) -> bool:
+def test_deploy_cert(plugin: common.Proxy, temp_dir: str, domains: list[str]) -> bool:
     """Tests deploy_cert returning True if the tests are successful"""
     cert = crypto_util.make_self_signed_cert(util.KEY, domains)
     cert_path = os.path.join(temp_dir, "cert.pem")
@@ -187,7 +183,7 @@ def test_enhancements(plugin: common.Proxy, domains: Iterable[str]) -> bool:
                      "enhancements")
         return False
 
-    domains_and_info: List[Tuple[str, List[bool]]] = [(domain, []) for domain in domains]
+    domains_and_info: list[tuple[str, list[bool]]] = [(domain, []) for domain in domains]
 
     for domain, info in domains_and_info:
         try:
@@ -390,7 +386,7 @@ def _fake_dns_resolution(resolved_ip: str) -> Generator[None, None, None]:
     """Monkey patch urllib3 to make any hostname be resolved to the provided IP"""
     _original_create_connection = connection.create_connection
 
-    def _patched_create_connection(address: Tuple[str, int],
+    def _patched_create_connection(address: tuple[str, int],
                                    *args: Any, **kwargs: Any) -> socket.socket:
         _, port = address
         return _original_create_connection((resolved_ip, port), *args, **kwargs)
diff --git a/certbot-compatibility-test/src/certbot_compatibility_test/validator.py b/certbot-compatibility-test/src/certbot_compatibility_test/validator.py
index fc35c8b9c..1e1139514 100644
--- a/certbot-compatibility-test/src/certbot_compatibility_test/validator.py
+++ b/certbot-compatibility-test/src/certbot_compatibility_test/validator.py
@@ -5,7 +5,6 @@ import socket
 from typing import cast
 from typing import Mapping
 from typing import Optional
-from typing import Tuple
 from typing import Union
 
 from cryptography import x509
@@ -146,7 +145,7 @@ def _probe_sni(name: bytes, host: bytes, port: int = 443) -> x509.Certificate:
     # Enables multi-path probing (selection
     # of source interface). See `socket.creation_connection` for more
     # info. Available only in Python 2.7+.
-    source_address: Tuple[str, int] = ('', 0)
+    source_address: tuple[str, int] = ('', 0)
     socket_kwargs = {'source_address': source_address}
 
     try:
@@ -157,7 +156,7 @@ def _probe_sni(name: bytes, host: bytes, port: int = 443) -> x509.Certificate:
                 source_address[1]
             ) if any(source_address) else ""
         )
-        socket_tuple: Tuple[bytes, int] = (host, port)
+        socket_tuple: tuple[bytes, int] = (host, port)
         sock = socket.create_connection(socket_tuple, **socket_kwargs)  # type: ignore[arg-type]
     except OSError as error:
         raise acme_errors.Error(error)
diff --git a/certbot-dns-cloudflare/src/certbot_dns_cloudflare/_internal/dns_cloudflare.py b/certbot-dns-cloudflare/src/certbot_dns_cloudflare/_internal/dns_cloudflare.py
index 7a5c86cfd..25ce84171 100644
--- a/certbot-dns-cloudflare/src/certbot_dns_cloudflare/_internal/dns_cloudflare.py
+++ b/certbot-dns-cloudflare/src/certbot_dns_cloudflare/_internal/dns_cloudflare.py
@@ -2,8 +2,6 @@
 import logging
 from typing import Any
 from typing import Callable
-from typing import Dict
-from typing import List
 from typing import Optional
 from typing import cast
 
@@ -188,7 +186,7 @@ class _CloudflareClient:
         """
 
         zone_name_guesses = dns_common.base_domain_name_guesses(domain)
-        zones: List[Dict[str, Any]] = []
+        zones: list[dict[str, Any]] = []
         code = msg = None
 
         for zone_name in zone_name_guesses:
diff --git a/certbot-dns-google/src/certbot_dns_google/_internal/dns_google.py b/certbot-dns-google/src/certbot_dns_google/_internal/dns_google.py
index c0fd702e9..945021117 100644
--- a/certbot-dns-google/src/certbot_dns_google/_internal/dns_google.py
+++ b/certbot-dns-google/src/certbot_dns_google/_internal/dns_google.py
@@ -2,7 +2,6 @@
 import logging
 from typing import Any
 from typing import Callable
-from typing import Dict
 from typing import Optional
 from typing import cast
 
@@ -253,7 +252,7 @@ class _GoogleClient:
         except googleapiclient_errors.Error as e:
             logger.warning('Encountered error deleting TXT record: %s', e)
 
-    def get_existing_txt_rrset(self, zone_id: str, record_name: str) -> Optional[Dict[str, Any]]:
+    def get_existing_txt_rrset(self, zone_id: str, record_name: str) -> Optional[dict[str, Any]]:
         """
         Get existing TXT records from the RRset for the record name.
 
diff --git a/certbot-dns-google/src/certbot_dns_google/_internal/tests/dns_google_test.py b/certbot-dns-google/src/certbot_dns_google/_internal/tests/dns_google_test.py
index a72f5c479..e5c6b6380 100644
--- a/certbot-dns-google/src/certbot_dns_google/_internal/tests/dns_google_test.py
+++ b/certbot-dns-google/src/certbot_dns_google/_internal/tests/dns_google_test.py
@@ -2,7 +2,6 @@
 from __future__ import annotations
 import sys
 from typing import Optional
-from typing import Tuple
 import unittest
 from unittest import mock
 
@@ -103,7 +102,7 @@ class GoogleClientTest(unittest.TestCase):
     def _setUp_client_with_mock(self,
         zone_request_side_effect: list[dict[str, list[dict[str, str]]]],
         rrs_list_side_effect: Optional[Error] = None
-        ) -> Tuple['certbot_dns_google._internal.dns_google._GoogleClient', mock.MagicMock]:
+        ) -> tuple['certbot_dns_google._internal.dns_google._GoogleClient', mock.MagicMock]:
         from certbot_dns_google._internal.dns_google import _GoogleClient
 
         pwd = os.path.dirname(__file__)
diff --git a/certbot-dns-route53/src/certbot_dns_route53/_internal/dns_route53.py b/certbot-dns-route53/src/certbot_dns_route53/_internal/dns_route53.py
index d70ec9114..702d30a4e 100644
--- a/certbot-dns-route53/src/certbot_dns_route53/_internal/dns_route53.py
+++ b/certbot-dns-route53/src/certbot_dns_route53/_internal/dns_route53.py
@@ -4,11 +4,7 @@ import logging
 import time
 from typing import Any
 from typing import Callable
-from typing import DefaultDict
-from typing import Dict
 from typing import Iterable
-from typing import List
-from typing import Type
 from typing import cast
 
 import boto3
@@ -45,7 +41,7 @@ class Authenticator(common.Plugin, interfaces.Authenticator):
         super().__init__(*args, **kwargs)
         self.r53 = boto3.client("route53")
         self._attempt_cleanup = False
-        self._resource_records: DefaultDict[str, List[Dict[str, str]]] = \
+        self._resource_records: collections.defaultdict[str, list[dict[str, str]]] = \
             collections.defaultdict(list)
 
     def more_info(self) -> str:
@@ -56,7 +52,7 @@ class Authenticator(common.Plugin, interfaces.Authenticator):
         # This authenticator currently adds no extra arguments.
         pass
 
-    def auth_hint(self, failed_achalls: List[achallenges.AnnotatedChallenge]) -> str:
+    def auth_hint(self, failed_achalls: list[achallenges.AnnotatedChallenge]) -> str:
         return (
             'The Certificate Authority failed to verify the DNS TXT records created by '
             '--dns-route53. Ensure the above domains have their DNS hosted by AWS Route53.'
@@ -65,10 +61,10 @@ class Authenticator(common.Plugin, interfaces.Authenticator):
     def prepare(self) -> None:
         pass
 
-    def get_chall_pref(self, unused_domain: str) -> Iterable[Type[challenges.Challenge]]:
+    def get_chall_pref(self, unused_domain: str) -> Iterable[type[challenges.Challenge]]:
         return [challenges.DNS01]
 
-    def perform(self, achalls: List[AnnotatedChallenge]) -> List[challenges.ChallengeResponse]:
+    def perform(self, achalls: list[AnnotatedChallenge]) -> list[challenges.ChallengeResponse]:
         self._attempt_cleanup = True
 
         try:
@@ -86,7 +82,7 @@ class Authenticator(common.Plugin, interfaces.Authenticator):
             raise errors.PluginError("\n".join([str(e), INSTRUCTIONS]))
         return [achall.response(achall.account_key) for achall in achalls]
 
-    def cleanup(self, achalls: List[achallenges.AnnotatedChallenge]) -> None:
+    def cleanup(self, achalls: list[achallenges.AnnotatedChallenge]) -> None:
         if self._attempt_cleanup:
             for achall in achalls:
                 domain = achall.domain
diff --git a/certbot-nginx/src/certbot_nginx/_internal/configurator.py b/certbot-nginx/src/certbot_nginx/_internal/configurator.py
index d3b9a747c..ad57fe67f 100644
--- a/certbot-nginx/src/certbot_nginx/_internal/configurator.py
+++ b/certbot-nginx/src/certbot_nginx/_internal/configurator.py
@@ -11,15 +11,10 @@ import tempfile
 import time
 from typing import Any
 from typing import Callable
-from typing import Dict
 from typing import Iterable
-from typing import List
 from typing import Mapping
 from typing import Optional
 from typing import Sequence
-from typing import Set
-from typing import Tuple
-from typing import Type
 from typing import Union
 from typing import cast
 
@@ -119,8 +114,8 @@ class NginxConfigurator(common.Configurator):
 
         # List of vhosts configured per wildcard domain on this run.
         # used by deploy_cert() and enhance()
-        self._wildcard_vhosts: Dict[str, List[obj.VirtualHost]] = {}
-        self._wildcard_redirect_vhosts: Dict[str, List[obj.VirtualHost]] = {}
+        self._wildcard_vhosts: dict[str, list[obj.VirtualHost]] = {}
+        self._wildcard_redirect_vhosts: dict[str, list[obj.VirtualHost]] = {}
 
         # Add number of outstanding challenges
         self._chall_out = 0
@@ -286,7 +281,7 @@ class NginxConfigurator(common.Configurator):
         self.save_notes += "\tssl_certificate_key %s\n" % key_path
 
     def _choose_vhosts_wildcard(self, domain: str, prefer_ssl: bool,
-                                no_ssl_filter_port: Optional[str] = None) -> List[obj.VirtualHost]:
+                                no_ssl_filter_port: Optional[str] = None) -> list[obj.VirtualHost]:
         """Prompts user to choose vhosts to install a wildcard certificate for"""
         if prefer_ssl:
             vhosts_cache = self._wildcard_vhosts
@@ -337,13 +332,13 @@ class NginxConfigurator(common.Configurator):
     #######################
     # Vhost parsing methods
     #######################
-    def _choose_vhost_single(self, target_name: str) -> List[obj.VirtualHost]:
+    def _choose_vhost_single(self, target_name: str) -> list[obj.VirtualHost]:
         matches = self._get_ranked_matches(target_name)
         vhosts = [x for x in [self._select_best_name_match(matches)] if x is not None]
         return vhosts
 
     def choose_vhosts(self, target_name: str,
-                      create_if_no_match: bool = False) -> List[obj.VirtualHost]:
+                      create_if_no_match: bool = False) -> list[obj.VirtualHost]:
         """Chooses a virtual host based on the given domain name.
 
         .. note:: This makes the vhost SSL-enabled if it isn't already. Follows
@@ -387,7 +382,7 @@ class NginxConfigurator(common.Configurator):
 
         return vhosts
 
-    def ipv6_info(self, host: str, port: str) -> Tuple[bool, bool]:
+    def ipv6_info(self, host: str, port: str) -> tuple[bool, bool]:
         """Returns tuple of booleans (ipv6_active, ipv6only_present)
         ipv6_active is true if any server block listens ipv6 address in any port
 
@@ -462,7 +457,7 @@ class NginxConfigurator(common.Configurator):
                                            f"block for {domain}. Set the `server_name` directive "
                                            "to use the Nginx installer.")
 
-    def _get_ranked_matches(self, target_name: str) -> List[Dict[str, Any]]:
+    def _get_ranked_matches(self, target_name: str) -> list[dict[str, Any]]:
         """Returns a ranked list of vhosts that match target_name.
         The ranking gives preference to SSL vhosts.
 
@@ -497,7 +492,7 @@ class NginxConfigurator(common.Configurator):
         return cast(obj.VirtualHost, matches[0]['vhost'])
 
     def _rank_matches_by_name(self, vhost_list: Iterable[obj.VirtualHost],
-                              target_name: str) -> List[Dict[str, Any]]:
+                              target_name: str) -> list[dict[str, Any]]:
         """Returns a ranked list of vhosts from vhost_list that match target_name.
         This method should always be followed by a call to _select_best_name_match.
 
@@ -535,7 +530,7 @@ class NginxConfigurator(common.Configurator):
         return sorted(matches, key=lambda x: x['rank'])
 
     def _rank_matches_by_name_and_ssl(self, vhost_list: Iterable[obj.VirtualHost],
-                                      target_name: str) -> List[Dict[str, Any]]:
+                                      target_name: str) -> list[dict[str, Any]]:
         """Returns a ranked list of vhosts from vhost_list that match target_name.
         The ranking gives preference to SSLishness before name match level.
 
@@ -552,7 +547,7 @@ class NginxConfigurator(common.Configurator):
                 match['rank'] += NO_SSL_MODIFIER
         return sorted(matches, key=lambda x: x['rank'])
 
-    def choose_redirect_vhosts(self, target_name: str, port: str) -> List[obj.VirtualHost]:
+    def choose_redirect_vhosts(self, target_name: str, port: str) -> list[obj.VirtualHost]:
         """Chooses a single virtual host for redirect enhancement.
 
         Chooses the vhost most closely matching target_name that is
@@ -580,8 +575,8 @@ class NginxConfigurator(common.Configurator):
             vhosts = [x for x in [self._select_best_name_match(matches)]if x is not None]
         return vhosts
 
-    def choose_auth_vhosts(self, target_name: str) -> Tuple[List[obj.VirtualHost],
-                                                            List[obj.VirtualHost]]:
+    def choose_auth_vhosts(self, target_name: str) -> tuple[list[obj.VirtualHost],
+                                                            list[obj.VirtualHost]]:
         """Returns a list of HTTP and HTTPS vhosts with a server_name matching target_name.
 
         If no HTTP vhost exists, one will be cloned from the default vhost. If that fails, no HTTP
@@ -649,7 +644,7 @@ class NginxConfigurator(common.Configurator):
     def _vhost_listening_on_port_no_ssl(self, vhost: obj.VirtualHost, port: str) -> bool:
         return self._vhost_listening(vhost, port, False)
 
-    def _get_redirect_ranked_matches(self, target_name: str, port: str) -> List[Dict[str, Any]]:
+    def _get_redirect_ranked_matches(self, target_name: str, port: str) -> list[dict[str, Any]]:
         """Gets a ranked list of plaintextish port-listening vhosts matching target_name
 
         Filter all hosts for those listening on port without using ssl.
@@ -671,7 +666,7 @@ class NginxConfigurator(common.Configurator):
 
         return self._rank_matches_by_name(matching_vhosts, target_name)
 
-    def get_all_names(self) -> Set[str]:
+    def get_all_names(self) -> set[str]:
         """Returns all names found in the Nginx Configuration.
 
         :returns: All ServerNames, ServerAliases, and reverse DNS entries for
@@ -679,7 +674,7 @@ class NginxConfigurator(common.Configurator):
         :rtype: set
 
         """
-        all_names: Set[str] = set()
+        all_names: set[str] = set()
 
         for vhost in self.parser.get_vhosts():
             try:
@@ -709,7 +704,7 @@ class NginxConfigurator(common.Configurator):
 
         return util.get_filtered_names(all_names)
 
-    def _get_snakeoil_paths(self) -> Tuple[str, str]:
+    def _get_snakeoil_paths(self) -> tuple[str, str]:
         """Generate invalid certs that let us create ssl directives for Nginx"""
         # TODO: generate only once
         tmp_dir = os.path.join(self.config.work_dir, "snakeoil")
@@ -745,7 +740,7 @@ class NginxConfigurator(common.Configurator):
         # no addresses should have ssl turned on here
         assert not vhost.ssl
 
-        addrs_to_insert: List[obj.Addr] = [
+        addrs_to_insert: list[obj.Addr] = [
             obj.Addr.fromstring(f'{addr.get_addr()}:{https_port} ssl')
             for addr in vhost.addrs
             if addr.get_port() == str(http_port)
@@ -764,8 +759,8 @@ class NginxConfigurator(common.Configurator):
             if vhost.ipv4_enabled():
                 addrs_to_insert += [obj.Addr.fromstring(f'{https_port} ssl')]
 
-        addr_blocks: List[List[str]] = []
-        ipv6only_set_here: Set[Tuple[str, str]] = set()
+        addr_blocks: list[list[str]] = []
+        ipv6only_set_here: set[tuple[str, str]] = set()
         for addr in addrs_to_insert:
             host = addr.get_addr()
             port = addr.get_port()
@@ -809,12 +804,12 @@ class NginxConfigurator(common.Configurator):
     ##################################
     # enhancement methods (Installer)
     ##################################
-    def supported_enhancements(self) -> List[str]:
+    def supported_enhancements(self) -> list[str]:
         """Returns currently supported enhancements."""
         return ['redirect', 'ensure-http-header', 'staple-ocsp']
 
     def enhance(self, domain: str, enhancement: str,
-                options: Optional[Union[str, List[str]]] = None) -> None:
+                options: Optional[Union[str, list[str]]] = None) -> None:
         """Enhance configuration.
 
         :param str domain: domain to enhance
@@ -835,7 +830,7 @@ class NginxConfigurator(common.Configurator):
         test_redirect_block = _test_block_from_block(_redirect_block_for_domain(domain))
         return vhost.contains_list(test_redirect_block)
 
-    def _set_http_header(self, domain: str, header_substring: Union[str, List[str], None]) -> None:
+    def _set_http_header(self, domain: str, header_substring: Union[str, list[str], None]) -> None:
         """Enables header identified by header_substring on domain.
 
         If the vhost is listening plaintextishly, separates out the relevant
@@ -884,8 +879,8 @@ class NginxConfigurator(common.Configurator):
         self.parser.add_server_directives(
             vhost, redirect_block, insert_at_top=True)
 
-    def _split_block(self, vhost: obj.VirtualHost, only_directives: Optional[List[str]] = None
-                     ) -> Tuple[obj.VirtualHost, obj.VirtualHost]:
+    def _split_block(self, vhost: obj.VirtualHost, only_directives: Optional[list[str]] = None
+                     ) -> tuple[obj.VirtualHost, obj.VirtualHost]:
         """Splits this "virtual host" (i.e. this nginx server block) into
         separate HTTP and HTTPS blocks.
 
@@ -919,7 +914,7 @@ class NginxConfigurator(common.Configurator):
         return http_vhost, vhost
 
     def _enable_redirect(self, domain: str,
-                         unused_options: Optional[Union[str, List[str]]]) -> None:
+                         unused_options: Optional[Union[str, list[str]]]) -> None:
         """Redirect all equivalent HTTP traffic to ssl_vhost.
 
         If the vhost is listening plaintextishly, separate out the
@@ -976,7 +971,7 @@ class NginxConfigurator(common.Configurator):
                 self.DEFAULT_LISTEN_PORT, vhost.filep)
 
     def _enable_ocsp_stapling(self, domain: str,
-                              chain_path: Optional[Union[str, List[str]]]) -> None:
+                              chain_path: Optional[Union[str, list[str]]]) -> None:
         """Include OCSP response in TLS handshake
 
         :param str domain: domain to enable OCSP response for
@@ -1075,7 +1070,7 @@ class NginxConfigurator(common.Configurator):
                 "Unable to run %s -V" % self.conf('ctl'))
         return text
 
-    def get_version(self) -> Tuple[int, ...]:
+    def get_version(self) -> tuple[int, ...]:
         """Return version of Nginx Server.
 
         Version is returned as tuple. (ie. 2.4.7 = (2, 4, 7))
@@ -1133,7 +1128,7 @@ class NginxConfigurator(common.Configurator):
         """
         text = self._nginx_version()
 
-        matches: List[str] = re.findall(r"running with OpenSSL ([^ ]+) ", text)
+        matches: list[str] = re.findall(r"running with OpenSSL ([^ ]+) ", text)
         if not matches:
             matches = re.findall(r"built with OpenSSL ([^ ]+) ", text)
             if not matches:
@@ -1225,13 +1220,13 @@ class NginxConfigurator(common.Configurator):
     ###########################################################################
     # Challenges Section for Authenticator
     ###########################################################################
-    def get_chall_pref(self, unused_domain: str) -> List[Type[challenges.Challenge]]:
+    def get_chall_pref(self, unused_domain: str) -> list[type[challenges.Challenge]]:
         """Return list of challenge preferences."""
         return [challenges.HTTP01]
 
     # Entry point in main.py for performing challenges
-    def perform(self, achalls: List[achallenges.AnnotatedChallenge]
-                ) -> List[challenges.ChallengeResponse]:
+    def perform(self, achalls: list[achallenges.AnnotatedChallenge]
+                ) -> list[challenges.ChallengeResponse]:
         """Perform the configuration related challenge.
 
         This function currently assumes all challenges will be fulfilled.
@@ -1240,7 +1235,7 @@ class NginxConfigurator(common.Configurator):
 
         """
         self._chall_out += len(achalls)
-        responses: List[Optional[challenges.ChallengeResponse]] = [None] * len(achalls)
+        responses: list[Optional[challenges.ChallengeResponse]] = [None] * len(achalls)
         http_doer = http_01.NginxHttp01(self)
 
         for i, achall in enumerate(achalls):
@@ -1266,7 +1261,7 @@ class NginxConfigurator(common.Configurator):
         return [response for response in responses if response]
 
     # called after challenges are performed
-    def cleanup(self, achalls: List[achallenges.AnnotatedChallenge]) -> None:
+    def cleanup(self, achalls: list[achallenges.AnnotatedChallenge]) -> None:
         """Revert all challenges."""
         self._chall_out -= len(achalls)
 
@@ -1276,13 +1271,13 @@ class NginxConfigurator(common.Configurator):
             self.restart()
 
 
-def _test_block_from_block(block: List[Any]) -> List[Any]:
+def _test_block_from_block(block: list[Any]) -> list[Any]:
     test_block = nginxparser.UnspacedList(block)
     parser.comment_directive(test_block, 0)
     return test_block[:-1]
 
 
-def _redirect_block_for_domain(domain: str) -> List[Any]:
+def _redirect_block_for_domain(domain: str) -> list[Any]:
     updated_domain = domain
     match_symbol = '='
     if util.is_wildcard_domain(domain):
diff --git a/certbot-nginx/src/certbot_nginx/_internal/constants.py b/certbot-nginx/src/certbot_nginx/_internal/constants.py
index 57bf55fad..6fa3c7270 100644
--- a/certbot-nginx/src/certbot_nginx/_internal/constants.py
+++ b/certbot-nginx/src/certbot_nginx/_internal/constants.py
@@ -1,7 +1,6 @@
 """nginx plugin constants."""
 import platform
 from typing import Any
-from typing import Dict
 
 FREEBSD_DARWIN_SERVER_ROOT = "/usr/local/etc/nginx"
 LINUX_SERVER_ROOT = "/etc/nginx"
@@ -14,7 +13,7 @@ elif platform.system() in ('NetBSD',):
 else:
     server_root_tmp = LINUX_SERVER_ROOT
 
-CLI_DEFAULTS: Dict[str, Any] = {
+CLI_DEFAULTS: dict[str, Any] = {
     "server_root": server_root_tmp,
     "ctl": "nginx",
     "sleep_seconds": 1
diff --git a/certbot-nginx/src/certbot_nginx/_internal/display_ops.py b/certbot-nginx/src/certbot_nginx/_internal/display_ops.py
index 3a0fa67ff..1efb75e7f 100644
--- a/certbot-nginx/src/certbot_nginx/_internal/display_ops.py
+++ b/certbot-nginx/src/certbot_nginx/_internal/display_ops.py
@@ -1,7 +1,6 @@
 """Contains UI methods for Nginx operations."""
 import logging
 from typing import Iterable
-from typing import List
 from typing import Optional
 
 from certbot.display import util as display_util
@@ -10,7 +9,7 @@ from certbot_nginx._internal.obj import VirtualHost
 logger = logging.getLogger(__name__)
 
 
-def select_vhost_multiple(vhosts: Optional[Iterable[VirtualHost]]) -> List[VirtualHost]:
+def select_vhost_multiple(vhosts: Optional[Iterable[VirtualHost]]) -> list[VirtualHost]:
     """Select multiple Vhosts to install the certificate for
     :param vhosts: Available Nginx VirtualHosts
     :type vhosts: :class:`list` of type `~obj.Vhost`
@@ -32,7 +31,7 @@ def select_vhost_multiple(vhosts: Optional[Iterable[VirtualHost]]) -> List[Virtu
     return []
 
 
-def _reversemap_vhosts(names: Iterable[str], vhosts: Iterable[VirtualHost]) -> List[VirtualHost]:
+def _reversemap_vhosts(names: Iterable[str], vhosts: Iterable[VirtualHost]) -> list[VirtualHost]:
     """Helper function for select_vhost_multiple for mapping string
     representations back to actual vhost objects"""
     return_vhosts = []
diff --git a/certbot-nginx/src/certbot_nginx/_internal/http_01.py b/certbot-nginx/src/certbot_nginx/_internal/http_01.py
index 5f450782a..9ee0cb409 100644
--- a/certbot-nginx/src/certbot_nginx/_internal/http_01.py
+++ b/certbot-nginx/src/certbot_nginx/_internal/http_01.py
@@ -2,7 +2,6 @@
 
 import logging
 from typing import Any
-from typing import List
 from typing import Optional
 from typing import TYPE_CHECKING
 
@@ -47,7 +46,7 @@ class NginxHttp01(common.ChallengePerformer):
         self.challenge_conf = os.path.join(
             configurator.config.config_dir, "le_http_01_cert_challenge.conf")
 
-    def perform(self) -> List[KeyAuthorizationChallengeResponse]:
+    def perform(self) -> list[KeyAuthorizationChallengeResponse]:
         """Perform a challenge on Nginx.
 
         :returns: list of :class:`acme.challenges.KeyAuthorizationChallengeResponse`
@@ -142,12 +141,12 @@ class NginxHttp01(common.ChallengePerformer):
         with open(self.challenge_conf, "w", encoding="utf-8") as new_conf:
             nginxparser.dump(config, new_conf)
 
-    def _default_listen_addresses(self) -> List[Addr]:
+    def _default_listen_addresses(self) -> list[Addr]:
         """Finds addresses for a challenge block to listen on.
         :returns: list of :class:`certbot_nginx._internal.obj.Addr` to apply
         :rtype: list
         """
-        addresses: List[Addr] = []
+        addresses: list[Addr] = []
         default_addr = "%s" % self.configurator.config.http01_port
         ipv6_addr = "[::]:{0}".format(
             self.configurator.config.http01_port)
@@ -175,7 +174,7 @@ class NginxHttp01(common.ChallengePerformer):
     def _get_validation_path(self, achall: KeyAuthorizationAnnotatedChallenge) -> str:
         return os.sep + os.path.join(challenges.HTTP01.URI_ROOT_PATH, achall.chall.encode("token"))
 
-    def _make_server_block(self, achall: KeyAuthorizationAnnotatedChallenge) -> List[Any]:
+    def _make_server_block(self, achall: KeyAuthorizationAnnotatedChallenge) -> list[Any]:
         """Creates a server block for a challenge.
 
         :param achall: Annotated HTTP-01 challenge
@@ -199,7 +198,7 @@ class NginxHttp01(common.ChallengePerformer):
         return [['server'], block]
 
     def _location_directive_for_achall(self, achall: KeyAuthorizationAnnotatedChallenge
-                                       ) -> List[Any]:
+                                       ) -> list[Any]:
         validation = achall.validation(achall.account_key)
         validation_path = self._get_validation_path(achall)
 
@@ -209,7 +208,7 @@ class NginxHttp01(common.ChallengePerformer):
         return location_directive
 
     def _make_or_mod_server_block(self, achall: KeyAuthorizationAnnotatedChallenge
-                                  ) -> Optional[List[Any]]:
+                                  ) -> Optional[list[Any]]:
         """Modifies server blocks to respond to a challenge. Returns a new HTTP server block
            to add to the configuration if an existing one can't be found.
 
@@ -222,7 +221,7 @@ class NginxHttp01(common.ChallengePerformer):
         """
         http_vhosts, https_vhosts = self.configurator.choose_auth_vhosts(achall.domain)
 
-        new_vhost: Optional[List[Any]] = None
+        new_vhost: Optional[list[Any]] = None
         if not http_vhosts:
             # Couldn't find either a matching name+port server block
             # or a port+default_server block, so create a dummy block
diff --git a/certbot-nginx/src/certbot_nginx/_internal/nginxparser.py b/certbot-nginx/src/certbot_nginx/_internal/nginxparser.py
index b800961c7..e82329717 100644
--- a/certbot-nginx/src/certbot_nginx/_internal/nginxparser.py
+++ b/certbot-nginx/src/certbot_nginx/_internal/nginxparser.py
@@ -8,10 +8,8 @@ from typing import Any
 from typing import IO
 from typing import Iterable
 from typing import Iterator
-from typing import List
 from typing import overload
 from typing import SupportsIndex
-from typing import Tuple
 from typing import Union
 
 from pyparsing import Combine
@@ -76,17 +74,17 @@ class RawNginxParser:
         """Returns the parsed tree."""
         return self.script.parseString(self.source)
 
-    def as_list(self) -> List[Any]:
+    def as_list(self) -> list[Any]:
         """Returns the parsed tree as a list."""
         return self.parse().asList()
 
 
 class RawNginxDumper:
     """A class that dumps nginx configuration from the provided tree."""
-    def __init__(self, blocks: List[Any]) -> None:
+    def __init__(self, blocks: list[Any]) -> None:
         self.blocks = blocks
 
-    def __iter__(self, blocks: typing.Optional[List[Any]] = None) -> Iterator[str]:
+    def __iter__(self, blocks: typing.Optional[list[Any]] = None) -> Iterator[str]:
         """Iterates the dumped nginx content."""
         blocks = blocks or self.blocks
         for b0 in blocks:
@@ -120,7 +118,7 @@ def spacey(x: Any) -> bool:
     return (isinstance(x, str) and x.isspace()) or x == ''
 
 
-class UnspacedList(List[Any]):
+class UnspacedList(list[Any]):
     """Wrap a list [of lists], making any whitespace entries magically invisible"""
 
     def __init__(self, list_source: Iterable[Any]) -> None:
@@ -142,15 +140,15 @@ class UnspacedList(List[Any]):
                     super().__delitem__(i)
 
     @overload
-    def _coerce(self, inbound: None) -> Tuple[None, None]: ...
+    def _coerce(self, inbound: None) -> tuple[None, None]: ...
 
     @overload
-    def _coerce(self, inbound: str) -> Tuple[str, str]: ...
+    def _coerce(self, inbound: str) -> tuple[str, str]: ...
 
     @overload
-    def _coerce(self, inbound: List[Any]) -> Tuple["UnspacedList", List[Any]]: ...
+    def _coerce(self, inbound: list[Any]) -> tuple["UnspacedList", list[Any]]: ...
 
-    def _coerce(self, inbound: Any) -> Tuple[Any, Any]:
+    def _coerce(self, inbound: Any) -> tuple[Any, Any]:
         """
         Coerce some inbound object to be appropriately usable in this object
 
@@ -191,7 +189,7 @@ class UnspacedList(List[Any]):
         super().extend(item)
         self.dirty = True
 
-    def __add__(self, other: List[Any]) -> "UnspacedList":
+    def __add__(self, other: list[Any]) -> "UnspacedList":
         new_list = copy.deepcopy(self)
         new_list.extend(other)
         new_list.dirty = True
diff --git a/certbot-nginx/src/certbot_nginx/_internal/obj.py b/certbot-nginx/src/certbot_nginx/_internal/obj.py
index 77db56a56..a80a531e7 100644
--- a/certbot-nginx/src/certbot_nginx/_internal/obj.py
+++ b/certbot-nginx/src/certbot_nginx/_internal/obj.py
@@ -1,10 +1,8 @@
 """Module contains classes used by the Nginx Configurator."""
 import re
 from typing import Any
-from typing import List
 from typing import Optional
 from typing import Sequence
-from typing import Set
 from typing import Union
 
 from certbot.plugins import common
@@ -178,7 +176,7 @@ class VirtualHost:
     """
 
     def __init__(self, filep: str, addrs: Sequence[Addr], ssl: bool, enabled: bool,
-                 names: Set[str], raw: List[Any], path: List[int]) -> None:
+                 names: set[str], raw: list[Any], path: list[int]) -> None:
         """Initialize a VH."""
         self.filep = filep
         self.addrs = addrs
@@ -226,7 +224,7 @@ class VirtualHost:
         found = _find_directive(self.raw, ADD_HEADER_DIRECTIVE, header_name)
         return found is not None
 
-    def contains_list(self, test: List[Any]) -> bool:
+    def contains_list(self, test: list[Any]) -> bool:
         """Determine if raw server block contains test list at top level
         """
         for i in range(0, len(self.raw) - len(test) + 1):
@@ -265,7 +263,7 @@ class VirtualHost:
                 https="Yes" if self.ssl else "No"))
 
 
-def _find_directive(directives: Optional[Union[str, List[Any]]], directive_name: str,
+def _find_directive(directives: Optional[Union[str, list[Any]]], directive_name: str,
                     match_content: Optional[Any] = None) -> Optional[Any]:
     """Find a directive of type directive_name in directives. If match_content is given,
        Searches for `match_content` in the directive arguments.
diff --git a/certbot-nginx/src/certbot_nginx/_internal/parser.py b/certbot-nginx/src/certbot_nginx/_internal/parser.py
index 4da91b0f6..eb5b67636 100644
--- a/certbot-nginx/src/certbot_nginx/_internal/parser.py
+++ b/certbot-nginx/src/certbot_nginx/_internal/parser.py
@@ -8,14 +8,10 @@ import re
 from typing import Any
 from typing import Callable
 from typing import cast
-from typing import Dict
 from typing import Iterable
-from typing import List
 from typing import Mapping
 from typing import Optional
 from typing import Sequence
-from typing import Set
-from typing import Tuple
 from typing import Union
 
 import pyparsing
@@ -39,7 +35,7 @@ class NginxParser:
     """
 
     def __init__(self, root: str) -> None:
-        self.parsed: Dict[str, UnspacedList] = {}
+        self.parsed: dict[str, UnspacedList] = {}
         self.root = os.path.abspath(root)
         self.config_root = self._find_config_root()
         self._http_path: str | None = None
@@ -108,12 +104,12 @@ class NginxParser:
             return os.path.normpath(os.path.join(self.root, path))
         return os.path.normpath(path)
 
-    def _build_addr_to_ssl(self) -> Dict[Tuple[str, str], bool]:
+    def _build_addr_to_ssl(self) -> dict[tuple[str, str], bool]:
         """Builds a map from address to whether it listens on ssl in any server block
         """
         servers = self._get_raw_servers()
 
-        addr_to_ssl: Dict[Tuple[str, str], bool] = {}
+        addr_to_ssl: dict[tuple[str, str], bool] = {}
         for server_list in servers.values():
             for server, _ in server_list:
                 # Parse the server block to save addr info
@@ -125,11 +121,11 @@ class NginxParser:
                     addr_to_ssl[addr_tuple] = addr.ssl or addr_to_ssl[addr_tuple]
         return addr_to_ssl
 
-    def _get_raw_servers(self) -> Dict[str, Union[List[Any], UnspacedList]]:
+    def _get_raw_servers(self) -> dict[str, Union[list[Any], UnspacedList]]:
         # pylint: disable=cell-var-from-loop
         """Get a map of unparsed all server blocks
         """
-        servers: Dict[str, Union[List[Any], nginxparser.UnspacedList]] = {}
+        servers: dict[str, Union[list[Any], nginxparser.UnspacedList]] = {}
         for filename, tree in self.parsed.items():
             servers[filename] = []
             srv = servers[filename]  # workaround undefined loop var in lambdas
@@ -144,7 +140,7 @@ class NginxParser:
                 servers[filename][i] = (new_server, path)
         return servers
 
-    def get_vhosts(self) -> List[obj.VirtualHost]:
+    def get_vhosts(self) -> list[obj.VirtualHost]:
         """Gets list of all 'virtual hosts' found in Nginx configuration.
         Technically this is a misnomer because Nginx does not have virtual
         hosts, it has 'server blocks'.
@@ -276,7 +272,7 @@ class NginxParser:
             except OSError:
                 logger.error("Could not open file for writing: %s", filename)
 
-    def parse_server(self, server: UnspacedList) -> Dict[str, Any]:
+    def parse_server(self, server: UnspacedList) -> dict[str, Any]:
         """Parses a list of server directives, accounting for global address sslishness.
 
         :param list server: list of directives in a server block
@@ -305,7 +301,7 @@ class NginxParser:
 
         return False
 
-    def add_server_directives(self, vhost: obj.VirtualHost, directives: List[Any],
+    def add_server_directives(self, vhost: obj.VirtualHost, directives: list[Any],
                               insert_at_top: bool = False) -> None:
         """Add directives to the server block identified by vhost.
 
@@ -327,7 +323,7 @@ class NginxParser:
         self._modify_server_directives(vhost,
             functools.partial(_add_directives, directives, insert_at_top))
 
-    def update_or_add_server_directives(self, vhost: obj.VirtualHost, directives: List[Any],
+    def update_or_add_server_directives(self, vhost: obj.VirtualHost, directives: list[Any],
                                         insert_at_top: bool = False) -> None:
         """Add or replace directives in the server block identified by vhost.
 
@@ -373,7 +369,7 @@ class NginxParser:
         vhost.raw = new_server
 
     def _modify_server_directives(self, vhost: obj.VirtualHost,
-                                  block_func: Callable[[List[Any]], None]) -> None:
+                                  block_func: Callable[[list[Any]], None]) -> None:
         filename = vhost.filep
         try:
             result = self.parsed[filename]
@@ -390,7 +386,7 @@ class NginxParser:
 
     def duplicate_vhost(self, vhost_template: obj.VirtualHost,
                         remove_singleton_listen_params: bool = False,
-                        only_directives: Optional[List[Any]] = None) -> obj.VirtualHost:
+                        only_directives: Optional[list[Any]] = None) -> obj.VirtualHost:
         """Duplicate the vhost in the configuration files.
 
         :param :class:`~certbot_nginx._internal.obj.VirtualHost` vhost_template: The vhost
@@ -443,7 +439,7 @@ class NginxParser:
         return new_vhost
 
 
-def _parse_ssl_options(ssl_options: Optional[str]) -> List[UnspacedList]:
+def _parse_ssl_options(ssl_options: Optional[str]) -> list[UnspacedList]:
     if ssl_options is not None:
         try:
             with open(ssl_options, "r", encoding="utf-8") as _file:
@@ -458,9 +454,9 @@ def _parse_ssl_options(ssl_options: Optional[str]) -> List[UnspacedList]:
     return UnspacedList([])
 
 
-def _do_for_subarray(entry: List[Any], condition: Callable[[List[Any]], bool],
-                     func: Callable[[List[Any], List[int]], None],
-                     path: Optional[List[int]] = None) -> None:
+def _do_for_subarray(entry: list[Any], condition: Callable[[list[Any]], bool],
+                     func: Callable[[list[Any], list[int]], None],
+                     path: Optional[list[int]] = None) -> None:
     """Executes a function for a subarray of a nested array if it matches
     the given condition.
 
@@ -479,7 +475,7 @@ def _do_for_subarray(entry: List[Any], condition: Callable[[List[Any]], bool],
                 _do_for_subarray(item, condition, func, path + [index])
 
 
-def get_best_match(target_name: str, names: Iterable[str]) -> Tuple[Optional[str], Optional[str]]:
+def get_best_match(target_name: str, names: Iterable[str]) -> tuple[Optional[str], Optional[str]]:
     """Finds the best match for target_name out of names using the Nginx
     name-matching rules (exact > longest wildcard starting with * >
     longest wildcard ending with * > regex).
@@ -595,7 +591,7 @@ def _is_ssl_on_directive(entry: Any) -> bool:
             entry[1] == 'on')
 
 
-def _add_directives(directives: List[Any], insert_at_top: bool,
+def _add_directives(directives: list[Any], insert_at_top: bool,
                     block: UnspacedList) -> None:
     """Adds directives to a config block."""
     for directive in directives:
@@ -604,7 +600,7 @@ def _add_directives(directives: List[Any], insert_at_top: bool,
         block.append(nginxparser.UnspacedList('\n'))
 
 
-def _update_or_add_directives(directives: List[Any], insert_at_top: bool,
+def _update_or_add_directives(directives: list[Any], insert_at_top: bool,
                               block: UnspacedList) -> None:
     """Adds or replaces directives in a config block."""
     for directive in directives:
@@ -783,8 +779,8 @@ def _remove_directives(directive_name: str, match_func: Callable[[Any], bool],
         del block[location]
 
 
-def _apply_global_addr_ssl(addr_to_ssl: Mapping[Tuple[str, str], bool],
-                           parsed_server: Dict[str, Any]) -> None:
+def _apply_global_addr_ssl(addr_to_ssl: Mapping[tuple[str, str], bool],
+                           parsed_server: dict[str, Any]) -> None:
     """Apply global sslishness information to the parsed server block
     """
     for addr in parsed_server['addrs']:
@@ -793,16 +789,16 @@ def _apply_global_addr_ssl(addr_to_ssl: Mapping[Tuple[str, str], bool],
             parsed_server['ssl'] = True
 
 
-def _parse_server_raw(server: UnspacedList) -> Dict[str, Any]:
+def _parse_server_raw(server: UnspacedList) -> dict[str, Any]:
     """Parses a list of server directives.
 
     :param list server: list of directives in a server block
     :rtype: dict
 
     """
-    addrs: Set[obj.Addr] = set()
+    addrs: set[obj.Addr] = set()
     ssl: bool = False
-    names: Set[str] = set()
+    names: set[str] = set()
 
     apply_ssl_to_all_addrs = False
 
diff --git a/certbot-nginx/src/certbot_nginx/_internal/parser_obj.py b/certbot-nginx/src/certbot_nginx/_internal/parser_obj.py
index d55fb7305..acd80da58 100644
--- a/certbot-nginx/src/certbot_nginx/_internal/parser_obj.py
+++ b/certbot-nginx/src/certbot_nginx/_internal/parser_obj.py
@@ -9,11 +9,8 @@ import logging
 from typing import Any
 from typing import Callable
 from typing import Iterator
-from typing import List
 from typing import Optional
 from typing import Sequence
-from typing import Tuple
-from typing import Type
 
 from certbot import errors
 
@@ -32,12 +29,12 @@ class Parsable:
     __metaclass__ = abc.ABCMeta
 
     def __init__(self, parent: Optional["Parsable"] = None):
-        self._data: List[Any] = []
+        self._data: list[Any] = []
         self._tabs = None
         self.parent = parent
 
     @classmethod
-    def parsing_hooks(cls) -> Tuple[Type["Block"], Type["Sentence"], Type["Statements"]]:
+    def parsing_hooks(cls) -> tuple[type["Block"], type["Sentence"], type["Statements"]]:
         """Returns object types that this class should be able to `parse` recursively.
         The order of the objects indicates the order in which the parser should
         try to parse each subitem.
@@ -57,7 +54,7 @@ class Parsable:
         raise NotImplementedError()
 
     @abc.abstractmethod
-    def parse(self, raw_list: List[Any], add_spaces: bool = False) -> None:
+    def parse(self, raw_list: list[Any], add_spaces: bool = False) -> None:
         """ Loads information into this object from underlying raw_list structure.
         Each Parsable object might make different assumptions about the structure of
         raw_list.
@@ -108,7 +105,7 @@ class Parsable:
         """
         raise NotImplementedError()
 
-    def dump(self, include_spaces: bool = False) -> List[Any]:
+    def dump(self, include_spaces: bool = False) -> list[Any]:
         """ Dumps back to pyparsing-like list tree. The opposite of `parse`.
 
         Note: if this object has not been modified, `dump` with `include_spaces=True`
@@ -153,7 +150,7 @@ class Statements(Parsable):
         if self.parent is not None:
             self._trailing_whitespace = "\n" + self.parent.get_tabs()
 
-    def parse(self, raw_list: List[Any], add_spaces: bool = False) -> None:
+    def parse(self, raw_list: list[Any], add_spaces: bool = False) -> None:
         """ Parses a list of statements.
         Expects all elements in `raw_list` to be parseable by `type(self).parsing_hooks`,
         with an optional whitespace string at the last index of `raw_list`.
@@ -173,7 +170,7 @@ class Statements(Parsable):
             return self._data[0].get_tabs()
         return ""
 
-    def dump(self, include_spaces: bool = False) -> List[Any]:
+    def dump(self, include_spaces: bool = False) -> list[Any]:
         """ Dumps this object by first dumping each statement, then appending its
         trailing whitespace (if `include_spaces` is set) """
         data = super().dump(include_spaces)
@@ -190,9 +187,9 @@ class Statements(Parsable):
     # ======== End overridden functions
 
 
-def _space_list(list_: Sequence[Any]) -> List[str]:
+def _space_list(list_: Sequence[Any]) -> list[str]:
     """ Inserts whitespace between adjacent non-whitespace tokens. """
-    spaced_statement: List[str] = []
+    spaced_statement: list[str] = []
     for i in reversed(range(len(list_))):
         spaced_statement.insert(0, list_[i])
         if i > 0 and not list_[i].isspace() and not list_[i-1].isspace():
@@ -217,7 +214,7 @@ class Sentence(Parsable):
         return (isinstance(lists, list) and len(lists) > 0 and
                 all(isinstance(elem, str) for elem in lists))
 
-    def parse(self, raw_list: List[Any], add_spaces: bool = False) -> None:
+    def parse(self, raw_list: list[Any], add_spaces: bool = False) -> None:
         """ Parses a list of string types into this object.
         If add_spaces is set, adds whitespace tokens between adjacent non-whitespace tokens."""
         if add_spaces:
@@ -240,7 +237,7 @@ class Sentence(Parsable):
             return
         self._data.insert(0, "\n" + tabs)
 
-    def dump(self, include_spaces: bool = False) -> List[Any]:
+    def dump(self, include_spaces: bool = False) -> list[Any]:
         """ Dumps this sentence. If include_spaces is set, includes whitespace tokens."""
         if not include_spaces:
             return self.words
@@ -258,7 +255,7 @@ class Sentence(Parsable):
     # ======== End overridden functions
 
     @property
-    def words(self) -> List[str]:
+    def words(self) -> list[str]:
         """ Iterates over words, but without spaces. Like Unspaced List. """
         return [word.strip("\"\'") for word in self._data if not word.isspace()]
 
@@ -311,7 +308,7 @@ class Block(Parsable):
         if expanded:
             yield from self.contents.iterate(expanded, match)
 
-    def parse(self, raw_list: List[Any], add_spaces: bool = False) -> None:
+    def parse(self, raw_list: list[Any], add_spaces: bool = False) -> None:
         """ Parses a list that resembles a block.
 
         The assumptions that this routine makes are:
diff --git a/certbot-nginx/src/certbot_nginx/_internal/tests/parser_test.py b/certbot-nginx/src/certbot_nginx/_internal/tests/parser_test.py
index 682a58230..52bc4456d 100644
--- a/certbot-nginx/src/certbot_nginx/_internal/tests/parser_test.py
+++ b/certbot-nginx/src/certbot_nginx/_internal/tests/parser_test.py
@@ -3,7 +3,6 @@ import glob
 import re
 import shutil
 import sys
-from typing import List
 
 import pytest
 
@@ -125,7 +124,7 @@ class NginxParserTest(util.NginxTest):
                    ([[[0], [3], [4]], [[5], [3], [0]]], [])]
 
         for mylist, result in mylists:
-            paths: List[List[int]] = []
+            paths: list[list[int]] = []
             parser._do_for_subarray(mylist,
                                     lambda x: isinstance(x, list) and
                                     len(x) >= 1 and
diff --git a/ruff.toml b/ruff.toml
index 5fb3b891f..5746249de 100644
--- a/ruff.toml
+++ b/ruff.toml
@@ -3,6 +3,9 @@ line-length = 100
 extend-exclude = ['tools', 'letstest']
 
 [lint]
+# Check for PEP 585 style annotations to prevent regressions in
+# https://github.com/certbot/certbot/issues/10195
+extend-select = ["UP006"]
 # Skip bare `except` rules (`E722`).
 # Skip ambiguous variable name (`E741`).
 ignore = ["E722", "E741",]